


Casual Misunderstandings

by beastlybolt



Category: Supernatural
Genre: Alternate Universe, F/M, Friends With Benefits, Jealousy, Oral Sex, POV Alternating, Secrets, Teacher-Student Relationship, Vaginal Sex, sort of
Language: English
Status: In-Progress
Published: 2017-04-27
Updated: 2017-04-27
Packaged: 2018-10-24 17:14:32
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,849
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10746213
Author URL: https://archiveofourown.org/users/beastlybolt/pseuds/beastlybolt
Summary: You didn't have to bend over or flaunt yourself to get your teacher's attention, it just sort of happened. Treating eachother like equals, talking like old friends, bonding over similar interests. He was attractive, not bad to listen to and certainly not bad to look at.Problem is, he's the only one thinking it's more than just getting off.





	Casual Misunderstandings

**Author's Note:**

> female character is 18, a senior in highschool whereas Dean is 26 teaching at her highschool. if that's not your cup of tea that's 100% okay!

You didn't even have to wear a short skirt or make your cleavage stand out to get your math teacher's attention. It didn't take anything at all on your part, really. Being yourself, treating each other like equals, talking like old friends. It took a month, he was shoving his face into your crotch by noon after asking you to stay for lunch to ask you a 'question'.

"Winchester?" You knocked on the door that happened to have been left ajar, and checked the corner, Mister Winchester's usual spot where his desk sits. After not seeing him there you looked around to find him in what seemed to be a frustrated, confused state in the middle of the room where no desks lay. One hand in his pockets, the other rubbing over his face like he was scrubbing something off. The usual suit jacket and khakis gone, the replacement just a nice plain shirt that fit him a little too well, along with blue jeans. Sort of domestic, *comfy* look that really does him good on the eyes. "Hey. I uh, wasn't sure why you told me to come here so sorry for being a couple minutes late. I had to get lunch. The menu is crap." You rambled, unsure what mood he's in professional or casual. You've had exchanges that were straight to the point, and you've also stayed after class and missed your passing period just talking about cars or your favorite movies in common. 

Your teacher, not to your surprise, smiled and laughed. "I mean who coulda' thought lunch ladies could mess up pizza? I mean, it's pizza for crying out loud!" You shake your head, then collect yourself once again. "So, what did you say I had to come here for again?" Mister a Winchester had never told you in the first place, but you're anxious being all alone with the man. 

 

-

 

Dean took a breath. 'My little brother told me to go for the kill and just ask you out, but you're so hot just standing there, and my palms are sweating, and this is illegal, so so illegal but you like cars and old movies and you smell so good-'

"Uh? Winchester?" She grinned, waving her hand over Dean's face pretending to check if he's conscious.

_Idiot. You fucking idiot. You're only good at sex, not talking, not feelings, just touching. Touch her. Communicate with your hands. Do it. Do it!_

Dean exhaled a big short breath, wiping his stupid gross sweaty hands on his pant before placing them carefully onto her shoulders. 

"Please let me do this. If you don't like it I'll stop, but I need this at least once."

Dean saw her eyebrows pinch together, similar to what she does in his class when she doesn't understand something, can't quite put the puzzle pieces together. He doesn't let her be confused too long, shaky hands pulling her closer, closer, closer. Fuck she knows what's happening by now. Her eyes are closing, he's way past personal space now, tasting her breath- Shit, shit, shit-

Y/N's lips are smooth, wet. He saw her lick and bite them half a minute ago. It's not rushed, or filled with lust or tongue. It's just touching of the lips, light and experimental. Dean had never felt so weak in the knees. Oh God, is he falling over?

"Dude," Y/N pulled away in time to catch Dean, who was seconds away from tripping on absolutely nothing. "that good? Really? There wasn't even the slightest bit of tongue and you fall on me?" Y/N laughs, cupping the man's chin in her fingers. Dean's cheeks are bright, hot. He takes a couple of breaths. 

"Really took ah- lots of courage for me to do that. You have no idea how long-"

Fucking loud low groan just decides to come from his throats when Y/N begins peppering kisses along the nape of the neck, still holding him. 

"I-I heard you had somebody. From your friends in class," Dean tries to continue. Oh boy is it hard. "Th-they said you and Gabe were a thing. W-what were they- Jesus Christ Y/N stop," he laughed with a stuttered breath, halting your butterfly kisses to be a little more concentrated. 

"Don't start whatcha can't finish, Winchester," you scold raising one eyebrow.

"Don't look at me with that tone of eyebrow."

You blink. "What." 

"Nothing."

".... Can we go back to makin' out or what?"

Dean's heartbeat is so high he thinks he might need to get a doctor after lunch is over.

"Do you have a.. a dude? Or girl, no judgement, I just uh, need to know what I'm sign in' up for. I don't like cheating and I'm single, so-"

"I." Kiss. "Do not." Another kiss, much more wet lands on his cheek. "Have." "A guy." "Or girl." "In my-" That time it was just a straight up lick. "Life."

Dean stops shivering to register what you had just said.

"Good."

 

-

 

If some future wizard told you that you'd have your sexy, undeniable, unresistable math teacher's head between your legs within the hour you would've laughed in its' face. But here you are, struggling to breath normal and not push up onto 'Deans' (he told you to use his first name now) wiggly exploring tongue. Mister W- no, Dean is mouthing at you through your underwear ( _batman? seriously, Y/N?_ he had laughed unbelievably. _yes, and if you have a problem with it- no, baby that just proves me right for thinkin' you're the perfect woman_ he had winked and then clicked his tongue.) It took ten minutes, you came on his tongue and his fingers. After he kissed every inch of skin exposed (your shirt was slightly unbuttoned along with your pants and underwear pulled all the way down laying on your shins.) It was perfect. After an awkward moment of shuffling of clothes back onto your body, jiggly unsteady legs find the floor and you button up your shirt once more. 

Dean is insecure and shows it well on his face, but that all changes when he touches you again. He leans in, at first a slight brush of the lips, then eventually spiraling the kiss into a sweet hot make out session before the bell rings. It makes you two jump, his eyes immediately opening up and searching all around the room for any students. There are none so far. One more kiss can't do any harm.

"I'll be seein' you," you wink and smile, giving him a little wave. The older man refuses to let you go just yet, half jogging across the room to cup your little figure into his arms and just hold you.

"Same time, everyday. Please? I need more time with you. It doesn't have to be like- like this," he motions to nothing in particular, just the two of you and gives his best shiny puppy dog eyes. 

"You're _this_ horny all the time? Enough to do it everyday? Dude, just as bad as the guys my age." You laugh, but he doesn't laugh with you. "All right. I'll come over here whenever I can, _Dean_." 

Dean just nods, and cards his fingers through his hair.

Sam texts him just in time before kids start crowding the classroom, right in the same desk Y/N had came all over his goddamn face on. Jesus. Put it away, Dean. 

from: Sam

 

you follow my advice and ask her?

 

to: Sam

 

yeah, a version of that. don't know if she took it as a date or not.

 

from: Sam

 

dude, how does she not know? did you bend her over already? not exactly "date" material, Dean.

 

to: Sam 

 

I didn't know how else to go about it, okay? jesus  
please just trust me on this, I think she likes me back

 

Dean puts his phone away as the last bell rings and all the students sit on their desks.

 

-

 

He asked if it were an everyday thing, or if it could be. You said yes. 

So it was. Sometimes handjobs were given, sometimes head, and when you both had real sex the first time Dean was as enthusiastic as ever. Things would go as far as just sending naughty pictures during class and seeing him get worked up, or passing notes for promises of what's to come for lunch time when his room was empty save for a horny you and Dean. 

You could only trust your close friend with what's been happening.

"Oh my god! You did NOT bang Winchester. No. I refuse to believe it. Seriously? Really? Really? Seriously?"

"Jesus Christ! Keep your voice down," you hush when you turn to see if anyone is in the stalls of the bathroom. "Someone could hear you and he could get fired and I could get expelled."

"That's awfully naughty Y/N," your friend ignores everything you had just said. "So how big is he? Pinky length? Or like, his shoe size? I've seen them bad boys, and if it IS true that a guys YOU KNOW is the size of his foot, then honey you've got a big storm comin." She clicks her tongue and looks you up and down suggestively. You roll your eyes and sigh.

"He's big, yes," you confess, throwing up your arms for emphasis. "It's a lot of fun but, it's not love or whatever. We mess around everyday and promised to keep it secret. And that's exactly what I did," you point and look her in the eye. A threat.

"Alright, alright. I didn't hear a thing. I won't tell. But damn, you go girl he is sexy!"

"Yeah, he really is."

 

-

 

"So you two do it? On the daily? All the time? Shit Dean, didn't even know you had it in you. You two serious yet?"

Dean smiles wickedly down at his lap, picking the label off his beer and chuckles. "Yeah, Sammy it's getting good. And when I say good, I mean GOOD. I have trouble even walking up the stairs good!" 

Sam makes a face, scrunching up like he smelt something disgusting. "Dean, I don't need your gross details. You know it's legal for two consenting adults eighteen or older but, student/teacher is frowned upon. I'm the only person that knows?"

"Of course. Y/N wouldn't tell anybody. I trust her. In fact, I'm thinking of inviting her to this fancy schmancy restaurant out the road tomorrow night, she'll look real sexy in a dress-"

"Does she know you call her your girlfriend?" Sam butts in. Dean is annoyed, rolling his eyes and taking long sips of his beverage and then looks up.

"Yeah, Sammy, obviously. And the pope wears a funny hat. No shit she knows I told her we should do more than sex." 

"Dean have you made it clear? She could just think you're fooling around just for the sake of fooling around."

It sticks with Dean the rest of the night, what Sam said. Maybe he's right. Maybe she does think it's just a teacher-student-with-benefits.


End file.
